48: The Beauty of a Calculated Risk: Chamath Palihapitiya

Chamath Palihapitiya was running AOL's instant messaging business at age 27. Not long after, he took a gamble on Facebook.

Chamath Palihapitiya was running AOL's instant messaging business at age 27. Not long after, he took a gamble on Facebook.

Chamath Palihapitiya is one of the most sought-after investors in Silicon Valley. It's because he has a knack for figuring out how things work. At Facebook, he led the team that studied our online behavior and figured out how to grow that service from 50 million users when he joined in 2007, to 700 million users when he left four years later. 

Now as the CEO of venture investing firm Social Capital, he's working on something different: cracking the code to understand how tech is changing our world – and maybe make a few billion dollars in the process. It's quite a journey for Palihapitiya. He grew up poor, an immigrant from Sri Lanka, with a knack for numbers, a talent for gambling, and the proverbial deck stacked against him. 

I visited Palihapitiya at Social Capital's offices in Palo Alto, California to get an up-close look at how he thinks. One of his deepest insights? Getting the right answer is overrated. Real growth happens from examining our wrong answers. 

Fitting in is Overrated

Palihapitiya grew up in Canada after his family immigrated from Sri Lanka and was granted refugee status. The family always struggled financially, but he didn't feel extremely self-conscious about it; instead, he adapted. He remembers that middle-class friends in high school in Ottowa were eager to gamble away quarters and dollars during lunch-hour card games; Palihapitiya quickly figured out that he would make the most money by setting up the amateur casino and acting as the house.

"I would take that money during the week and I would kind of go to these charity casinos and play blackjack. And I was a card counter back then. So I'd be spinning up my money," he recalls. "I didn't have a bedroom. I didn't have a bed. I had a mattress, and we used to keep it in the closet of the hallway. I used to take it out, sleep in the living room, put it back."

Penciling Out the Downside

Years later, working at AOL, Palihapitiya did a deal to integrate instant messenger with a fledgeling product called Facebook. (He had wanted AOL to try to buy Facebook, but the company was too tangled up in legal drama.) Eventually the partnership unravelled, and Facebook's teenaged founder asked Palihapitiya if he wouldn't like to leave the venture firm where he had taken a job, and join the startup instead.

"I said, 'What is the distribution of outcomes at Facebook?' Most of the scenarios were less than [I would make at the venture firm], but there were a few scenarios where I could make a case that it could be equivalent to what I would make at Mayfield over a four-year period, and in a very small number of cases it would be in excess," he says. But even if it doesn't work out, he thought, "I will have met some of the smartest people in the world, and I'll be in the game. And I will have learned something about myself, whether I can do something at a really early-stage scale."

As it turned out, of course, Facebook was a pretty good bet for him.